This study is the first to systematically inquire into the lives of transgender men and women currently serving across the branches of the US military in the post-“Don’t Ask, Don’t Tell” (DADT) repeal era. We employed an interview protocol from a stratified convenience sample (n = 14) of clandestinely serving active duty, guard and reserve military members from the US Army, Navy, Air Force, and Marine Corps who self-identified as transgender or transsexual. Using phenomenology as a methodological foundation, we present a revelatory case study based on lived experiences from firsthand accounts furthering the collective understanding of gender dysphoria in a contemporary military context.